U.S. patent number 6,592,924 [Application Number 09/877,907] was granted by the patent office on 2003-07-15 for game-type flavoring agent.
This patent grant is currently assigned to Nestec S.A.. Invention is credited to Imre Blank, Christoph Cerny, Stephanie Devaud, Sven Heyland.
United States Patent |
6,592,924 |
Blank , et al. |
July 15, 2003 |
**Please see images for:
( Certificate of Correction ) ** |
Game-type flavoring agent
Abstract
A flavoring agent for enhancing or imparting game-type flavor in
food products, including a combination of an alkylphenol and
cyclohexanecarboxylic acid or an alkyl-substituted derivative
thereof, and methods for preparing such of flavoring compositions
and food products.
Inventors: |
Blank; Imre (Savigny,
CH), Cerny; Christoph (Winterthur, CH),
Devaud; Stephanie (Porsel, CH), Heyland; Sven
(Weiningen, CH) |
Assignee: |
Nestec S.A. (Vevey,
CH)
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Family
ID: |
33492180 |
Appl.
No.: |
09/877,907 |
Filed: |
June 8, 2001 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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PCTEP9908910 |
Dec 1, 1999 |
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Foreign Application Priority Data
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Dec 22, 1998 [EP] |
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98204369 |
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Current U.S.
Class: |
426/534; 426/2;
426/536; 426/538 |
Current CPC
Class: |
A23K
50/48 (20160501); A23L 27/203 (20160801); A23L
27/204 (20160801); A23L 27/26 (20160801) |
Current International
Class: |
A23K
1/18 (20060101); A23L 1/231 (20060101); A23L
1/226 (20060101); A23L 001/22 () |
Field of
Search: |
;426/534,2,533,536,538,623,635,650 |
References Cited
[Referenced By]
U.S. Patent Documents
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3922367 |
November 1975 |
Gorbatov et al. |
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Foreign Patent Documents
Other References
Fennema, O.R. ed., Food Chemistry, Third Edition, 1996, Marcel
Dekker, Inc., New York, p. 752.* .
N.G. Eider, "Analysis of Naphthenic Acid by Gas-Liquid
Chromatography," Journal of Paint Technology, vol. 42, No. 548, pp.
504-509, 1970. .
J.C. leffingwell et al., "Tobacco Flavoring for Smoking Products,"
R.J. Reynolds Tobacco Company, pp. 10-12, 1972. .
B.L. Oser et al., "Recent Progress in the Consideration of
Flavoring Ingredients Under the Food Additives Amendment, 11. GRAS
Substances," Food Technology, pp. 60-70, Feb. 1978. .
J.M. Bakke et al., "Volatile Compounds From the Red Deer (Cervus
Elaphus). Secretion From the Tail Gland," Journal of Chemical
Ecology, vol. 9, No. 4, pp. 513-520, 1983. .
J.M. Bakke et al., "Volatile Compounds From the Red Deer (Cervus
Elaphus). Substances Secreted Via the Urine," Comp. Biochem.
Physiol., vol. 97A, No. 3, pp. 427-431, 1990. .
J.K. Ha et al., "Volatile Alkylphenols and Thiophenol in
Species-related Characterizing Flavors of Red Meats," Journal of
Food Science, vol. 56, No. 5, pp. 1197-1202, 1991..
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Primary Examiner: Wong; Leslie
Attorney, Agent or Firm: Winston & Strawn
Parent Case Text
CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation of the US national phase
designation of PCT Application No. PCT/EP99/08910, filed Dec. 1,
1999, the disclosure of which is expressly incorporated by
reference herein.
Claims
What is claimed is:
1. A game-enhancing or imparting flavoring agent comprising a
combination of (a) at least one alkylphenol or isomer thereof, and
(b) at least one cyclohexanecarboxylic acid or alkyl-substituted
derivative thereof, wherein the ratio of (a) to (b) is 1:1 to 20:1
by weight and wherein the combination enhances or imparts a
game-type flavor to food products to which it is added.
2. The flavoring agent of claim 1, wherein the alkylphenol
comprises one or more of a para, ortho, or meta isomer of cresol,
ethylphenol, or propylphenol.
3. The flavoring agent of claim 1, further comprising a short chain
alkyl acid.
4. The flavoring agent of claim 3, wherein the short chain alkyl
acid comprises at least one of butyric or isovaleric acid.
5. The flavoring agent of claim 3, wherein the short chain alkyl
acid is present in an amount of about 80% to 99.9%.
6. The flavoring agent of claim 1, further comprising phenylacetic
acid.
7. The flavoring agent of claim 6, wherein the phenylacetic acid is
present in an amount of about 0.4% to 15%.
8. The flavoring agent of claim 1, which comprises greater than
0.1% to 10% by weight of a combination of cyclohexanecarboxylic
acid and p-cresol in order to obtain an agouti-flavor.
9. The flavoring agent of claim 8, further comprising 45% to 75% by
weight butyric acid, 22% to 42% by weight isovaleric acid, and up
to 3% by weight of phenylacetic acid.
10. The flavoring agent of claim 8, wherein the ratio of p-cresol
and cyclohexanecarboxylic acid to other acids is 0.2:99.8 to
20:80.
11. A culinary product comprising at least 0.1% by weight of the
flavoring agent of claim 1.
12. The culinary product of claim 11, which comprises 0.01% to 2%
p-cresol and 0.0005% to 2% cyclohexanecarboxylic acid.
13. A culinary product comprising a dosage of at least 1 mg/kg of
the flavoring agent of claim 1.
14. The flavoring agent of claim 1, comprising a dried mixture
formed from 1 percent to 10 percent of the mixture of an
alkylphenol, or an isomer thereof cyclohexanecarboxylic acid or an
alkyl-substituted derivative thereof, from 15% to 40% maltodextrin,
from 1% to 5% gum arabic, and from 50% to 80% water.
15. The flavoring agent of claim 14, the dried mixture has less
than about 2% water content and the ratio of (a) to (b) is 6:1.
16. The flavoring agent of claim 1, which comprises 0.94% to 10% by
weight of a combination of cyclohexanecarboxylic acid and p-cresol
to obtain an agouti-flavor.
17. A pet food comprising at least 0.1% by weight of the flavoring
agent of claim 1.
18. The pet food of claim 17, which comprises 0.01% to 2% p-cresol
and 0.0005% to 2% cyclohexanecarboxylic acid.
19. A pet food comprising a dosage of at least 1 mg/kg of the
flavoring agent of claim 1.
20. The flavoring agent of claim 1, wherein the ratio of (a) to (b)
is greater than 1:1 to 20:1 by weight.
Description
FIELD OF INVENTION
This invention relates to a flavoring agent intended for enhancing
or imparting game-type flavor in food products.
BACKGROUND OF THE INVENTION
Meat-like flavorings and their method of preparation are well
known. They can be produced, for example, by a thermal reaction
between the free amino groups of amino acids and/or of peptides,
and the carbonyl groups of reducing sugars. The combination of
flavor molecules in the right proportions and the resulting
mixtures represent another possibility to produce meat-like
flavors. These preparations are also known as "compounded flavors."
A combination of both approaches can also be applied to produce
meat-like flavors.
Compounds responsible for meat flavor in food products and commonly
used in compounded flavors are, for example, furfurylthiol,
2,5-dimethyl-4-hydroxy-3(2H)-furanone, methional,
2,3-diethyl-5-methylpyrazine, 2-methyl-3-furanthiol, furfural,
3-mercapto-2-butanone, maltol, sotolone, abhexone, butyric acid,
diacetyl, 2,3-pentandione. Although game-type flavoring compounds
have not yet been described, such compounds are desired to provide
or enhance the flavor of foodstuffs with a game-type flavor.
SUMMARY OF THE INVENTION
This invention provides a flavoring agent for enhancing or
imparting game-type flavor in food products, that includes a
combination of an alkylphenol and cyclohexanecarboxylic acid or an
alkyl-substituted derivative thereof.
Although cyclohexanecarboxylic acid is known as a flavor compound,
it has not been described as being useful in meat-like or game-type
flavors. Although alkylphenols are compounds widely found in
nature, there previously was no evidence, however, that
cyclohexanecarboxylic acid or alkylphenols, such as p-cresol, or an
isomer thereof, are particularly useful to achieve game-type flavor
notes. Nor are there any indications that the combination of both
compounds might be useful to achieve this goal.
To obtain a specific desired game-type flavor in one embodiment,
these two flavor compounds are preferably combined in a specific
ratio (alkylphenol to cyclohexanecarboxylic acid) of 1:1 to 20:1 by
weight. The flavoring agent may also contain a source of short
chain alkyl acids that contribute to reinforce sweaty and
animal-like notes to the overall flavor of the flavoring agent. The
flavoring agent may also contain phenylacetic acid to further
enhance the animal-like note. Thus, the flavoring agent is intended
to give culinary products an authentic game-specific flavor note
without using any meat extract, and may also be used to provide a
game-specific flavor note in pet foods. Another aspect of the
present invention is the use of this flavoring agent in flavor
blends or in any process for the preparation of game-flavored
products.
DETAILED DESCRIPTION OF THE INVENTION
As used herein, all percentages are given on the basis of weight,
except where specifically stated otherwise. Also, the term "flavor"
includes odor, aroma, or taste.
The flavoring agent includes a combination of an alkylphenol, or an
isomer thereof, and cyclohexanecarboxylic acid or its
alkyl-substituted derivatives, that may be mixed in a ratio of 1:1
to 20:1 by weight, and preferably in a ratio of about 6:1. The
alkyl group of an alkyl-substituted derivative of
cyclohexanecarboxylic acid can be, for example, methyl, ethyl, or
propyl located in position 2-, 3-, or 4 of the cycle. The
alkyl-substituted derivative can be a cis- or trans isomer or
mixtures thereof. The alkylphenol may preferably be one of the
three isomers: ortho, meta, or para of cresol, ethylphenol, or
propylphenol.
In a preferred embodiment, the flavoring agent may also contain one
or more of a source of short chain alkyl acids or a source of
phenylacetic acid. Short chain alkyl acids are preferably those
containing 4 to 6 carbons, such as butyric and isovaleric acid,
that can be added in an amount of about 80% to 99.9%, and
preferably 99.5%. Phenylacetic acid may be added in an amount of
about 0.4% to 15%.
The flavoring agent can be prepared by mixing its constitutive
compounds. The obtained mixture may be in a liquid or dried form.
In a preferred embodiment, the liquid flavoring agent may contain
p-cresol and cyclohexanecarboxylic acid in a ratio of 1:1 to 20:1.
The ratio of the mixture p-cresol and cyclohexanecarboxylic acid to
other acids is preferably 0.2:99.8 to 20:80. The dried flavoring
agent can be prepared by mixing about 1% to 10% of the liquid
flavoring agent with about 15% to 40% of maltodextrin and 1% to
In a preferred embodiment, the flavoring agent may have an
agouti-flavor note. Accordingly, the flavoring agent may have the
following composition (Table 1).
TABLE 1 Composition of an agouti-type flavoring agent Compound
Composition (%) Butyric acid 45-75 Isovaleric acid 22-42
Phenylacetic acid 0-3 p-Cresol/Cyclohexanecarboxylic acid 0.1-10
(ratio 1:1 to 20:1) Total 100
Thus, the flavoring agent is intended to give an authentic game or
meat-specific aroma note to culinary products, and may also be used
to provide a game-specific aroma note in pet foods. The flavoring
agent may be used directly in its liquid or dried form to enhance
or impart game-type flavor in culinary products. The amount of the
liquid form is preferably of about 0.05 to 5 g per kg of culinary
product or pet food product, and depends on the requisite degree of
aroma desired. The dried form of the flavoring agent can be used in
an amount of 0.2 to 50 g per kg.
Another aspect of the present invention is the use of this agent in
any process for the preparation of game-flavored food products.
Accordingly, the flavoring agent may be used in a process where
cystein and/or thiamine, a reducing sugar, and a plant protein
hydrolysate can be used for the basic meat-flavor. The amount of
added flavoring agent may be at least about 0.1%, and the
concentration in the final culinary product or pet food product is
preferably at least 1 mg/kg. After the thermal flavor reaction,
which is preferably carried out in a stirred reactor with
temperature control, the flavoring agent is added, either in its
liquid or dried form, and the resulting mixture is homogenized and
dried in a vacuum oven.
EXAMPLES
The following examples are given by way of illustration only and in
no way should be construed as limiting the subject matter of the
present application.
Example 1
Preparation of an Agouti-Type Flavoring Agent
A liquid agouti flavoring agent was prepared by mixing:
65% butyric acid 33% isovaleric acid 1.06% phenylacetic acid 0.84%
p-cresol 0.1% cyclohexanecarboxylic acid
100 mg of the mixture was then diluted in 1 L of hot water to
evaluate the flavor. The mixture had a very authentic smell and
taste of agouti.
A dried form of the flavoring agent was obtained by mixing 2 g of
the liquid flavoring agent, 32 g of maltodextrin, 6 g gum arabic
and 60 g of water. The mixture was then spray-dried up to an amount
of 2% humidity.
Example 2
Preparation of an Agouti Flavoring Composition
In order to prepare a flavoring composition, the following
ingredients were mixed:
Hydrolyzed plant protein 45% Water 45% IMP 4% Cystein HCl 0.75%
Thiamin 0.75% Xylose 1.5% Beef fat 2.75% Onion extract 0.25%
The mixture was then submitted to a browning reaction in an
autoclave at a temperature of about 105.degree. C. for about 2
hours. 1% of the liquid agouti flavoring agent, as obtained in
Example 1 was added. The obtained mixture was dried by means of a
vacuum oven.
The resulting powder can be used directly in water to prepare a
bouillon or to enhance agouti-flavor in culinary products.
Example 3
Agouti Flavored Bouillon
10 g of the flavoring composition obtained in example 2 was
dissolved in 1 L of hot water. The solution had an authentic agouti
flavor as perceived by smelling and tasting the sample.
Example 4
Bouillon With Agouti Flavor
A mixture of 370 g of maltodextrin, 190 g of salt, 100 g of yeast
extract, 90 g of dextrose, 80 g of starch, 65 g beef fat, 40 g of
sugar, 2 g citric acid and various condiments was prepared. 19 g of
this mixture, 1 g of salt, and 1 g of the spray-dried agouti
flavoring agent obtained as described in Example 1 were added to 1
L of hot water. The bouillon obtained had a specific agouti flavor
as perceived by smelling and tasting the sample.
Example 5
Game-Flavored Pet Food Preparation
A mixture was prepared from 73% poultry carcass, pig lungs, and
beef liver (ground), 16% wheat flour, 7% water, 2% dyes, 0.2%
liquid agouti flavoring as prepared in Example 1, vitamins, and
inorganic salts. This mixture was emulsified at 12.degree. C. and
extruded in the form of a pudding which was then cooked at a
temperature of 90.degree. C. The mixture was cooled to 30.degree.
C. and cut into chunks. 45% of these game flavored chunks were
mixed with 55% of a sauce prepared from 98% water, 1% dye, and 1%
guar gum. Tinplate cans were filled and sterilized at 125.degree.
C. for 40 min. This pet food had a pleasant game flavor as
perceived by smelling the sample.
It is to be understood that the invention is not to be limited to
the exact configuration as illustrated and described herein.
Accordingly, all expedient modifications readily attainable by one
of ordinary skill in the art from the disclosure set forth herein,
or by routine experimentation therefrom, are deemed to be within
the spirit and scope of the invention as defined by the appended
claims. It is to be understood that the invention is not to be
limited to the exact configuration as illustrated and described
herein. Accordingly, all expedient modifications readily attainable
by one of ordinary skill in the art from the disclosure set forth
herein, or by routine experimentation therefrom, are deemed to be
within the spirit and scope of the invention as defined by the
appended claims.
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